Comparing thermoplastics, thermosets & fibres, examples of condensation polymers, natural polymers including proteins, DNA, wood, silk, starch, cellulose

Doc Brown's GCSE/IGCSE/O Level KS4 science-CHEMISTRY Revision Notes

Oil, useful products, environmental problems, introduction to organic chemistry

11. Comparison of thermoplastic addition polymers, synthetic fibres from condensation polymers and thermosets

This further page on macromolecules-plastics describes the difference in formation of addition polymers like poly(chloroethene)/PVC and condensation polymers like Terylene and Nylon, all of which are thermosoftening polymers. The properties of thermosoftening polymers (thermoplastics) are compared with thermosetting polymers (thermosets). These revision notes on plastics and fibres should prove useful for the new AQA, Edexcel and OCR GCSE (91) chemistry science courses. These revision notes on the comparison of the structure and properties of thermoplastic polymers, thermosets and fibres should prove useful for the NEW AQA GCSE chemistry, Edexcel GCSE chemistry & OCR GCSE chemistry (Gateway & 21st Century) GCSE (91), (9-5) & (5-1) science courses.

Index of KS4 Science GCSE/IGCSE/O Level Chemistry Oil & Organic Chemistry revision notes pages: 1. Fossil Fuels & carbon Cycle : 2. Fractional distillation of crude oil & physical properties and uses of fractions, what makes a good fuel? : 3. ALKANES - saturated hydrocarbons, structure, uses, combustion : 4. Pollution, carbon monoxide, sulfur/nitrogen oxides, climate change-global warming, carbon footprint : 5. Alkenes - unsaturated hydrocarbons, structure and chemistry : 6. Cracking - a problem of supply and demand, other products : 7. Polymers, plastics, uses and problems : 8. Introduction to Organic Chemistry - Why so many series of organic compounds? : 9a. Alcohols, Ethanol, manufacture, physical properties & chemical reactions : 9b. Biofuels & alternative fuels, hydrogen, biogas, biodiesel : 10a. Carboxylic acids - chemistry and uses : 10b. Esters, chemistry and uses including perfumes : 11. Condensation polymers, Nylon & Terylene, comparing thermoplastics, fibres and thermosets : 12. Natural Molecules - carbohydrates - sugars - starch : 13. Amino acids, proteins, enzymes & chromatography : 14. Oils, fats, margarine and soaps : 15. Vitamins, drugs-analgesic medicines & food additives and aspects of cooking chemistry! : 16. Ozone destruction, CFC's and free radicals : Multiple Choice and Gap-Fill Quizzes: m/c QUIZ on Oil Products (GCSE/IGCSE easier-foundation-level) : m/c QUIZ on Oil Products (GCSE/IGCSE harder-higher-level) : IGCSE/GCSE m/c QUIZ on other Aspects of Organic Chemistry : and 3 Easy linked GCSE/IGCSE Oil Products word-fill worksheets

ALL my Advanced Level Organic Chemistry revision notes

11A. More on POLYMERS - synthetic macromolecules

Polymers are long chain molecule formed from lots of repeating units joined together by strong covalent bonds.

Modifying polymers, thermoplastics and thermosets

  • First some reminders from section 7. about addition polymers which were discussed in some detail.
  • As an example the formation of PVC is shown below.
    • , the long chain PVC molecules

    • and what the molecules look like in the structure of PVC or any other thermoplastic.

    • Although the PVC molecules look straight, in reality, the long molecules will be all twisted-jumbled up as in the thermoplastic diagram above (a bit spaghetti like!).

  • Advanced Chemistry Page Index and LinksThis is a typical addition polymer (formed by simple addition of monomer molecules), just like polythene and polystyrene etc. AND they are examples of thermoplastics, that is they can be heated and softened, reshaped and cooled to keep their new moulded shape.

  • Thermoplastic polymers (thermoplastics)
    • A molecular model for a thermoplastic

    • In thermoplastics the intermolecular forces between the polymer molecules are quite weak compared to the strong covalent bonds (C-C) holding the chain of atoms together.

    • Because the 'intermolecular bonding' is weak, this explains that when heated, these 'plastic' materials will soften quite easily, which is why they are called 'thermoplastic' and have relatively low softening points and melting points.

    • Even at room temperature the plastic is easily distorted because the polymer chains can slide over each other i.e. the external physical force applied on bending overcomes the intermolecular forces between the polymer molecules.

    • Despite their relative weakness, on controlled heating until they are quite soft (but NOT molten), they are readily extrusion moulded or drawn out into useful shapes which retain their new formation on cooling.

    • So, overall, thermoplastics are not that heat resistant or exceptionally rigid/strong - but their properties do vary quite widely e.g. poly(propene) and nylon can be drawn into strong fibres and both can be manufactured into quite strong and rigid forms.

    • See nylon and terylene

    • First a reminder that the use of a polymer mainly depends on its physical properties (which are derived from the polymers structure).

      • You can chemically modify polymers to change their physical properties to suit a particular use or application.

        • If you increase the chain length of the polymer molecules you increase the intermolecular forces between the chains so it is stronger and less flexible and has a higher softening/melting point.

        • If you shorten the average chain length the polymer has lower softening/melting and is easier to shape, and the plastic is more flexible.

        • Cross-linking, i.e. adding a cross-linking agent to the monomer/polymer mixture which forms strong chemical bonds between polymer chains is discussed below and this modification is most important when comparing thermosoftening plastics and thermosetting plastics. Cross

  • In thermosoftening plastics like poly(ethene), poly(propene) or poly(chloroethene) PVC, because the inter-molecular attractive forces between the chains are weak, the plastic softens when heated and hardens again when cooled.
    • It also means the polymer molecules can slide over each other especially when heated to their relatively low softening/melting points.
    • This means they can be easily stretched or moulded into any desired shape.
    • They are examples of thermoplastics (thermosoftening plastics), because they can be heated to make them softer - more plastic, reshape it e.g. in an injection mould system, and on cooling the plastic object retains its new shape - bottle, bowl, toy etc.
    • However it is possible to manufacture and process plastics in which the polymer chains are made to line up. This greatly increases the intermolecular forces between the 'aligned' polymer molecules and strong fibre strands of the plastic can be made.
    • Examples: The addition polymer poly(propene) and the condensation polymers nylon and Terylene.
  • Thermosoftening polymers like poly(ethene) and poly(propene) consist of individual, tangled polymer chains and melt relatively easily when they are heated. This contrasts with thermosetting polymers consist of polymer chains with strong cross-links between them and so they do not melt when they are heated.
  • When a thermosetting plastic is formed you not only get polymerisation to form long molecules, you also get chemical bonds formed between various points in one polymer chain molecule across to another polymer molecule.
    • These extra bonds are called cross-links and hold the linear polymer chains together in a much more rigid structure.
      • These cross links do not usually occur in the simpler addition polymerisations when thermoplastics like poly(ethene) and PVC are made.
    • Commercially, many thermosets consist of a partially polymerised (but not cross-linked) resin, which contains a cross-linking agent and a catalyst, so that when the mixture is exposed to air or a the mixture warmed, cross-linking polymerisation occurs and the hard thermoset is formed. This type of mixture is used to make fibre-glass reinforced structures e.g. light car bodies or the hulls of sailing boats and canoes.
  • These extra cross-linking covalent bonds formed between adjacent chains of the polymers change the physical properties considerably and thermoset polymers have much higher high melting points (giving greater heat resistance and thermal stability) as well as greatly increased strength and rigidity.
    • Compared to thermosoftening plastics, thermoset polymers do not soften or melt and only break down at much higher temperatures compared to the softening/melting points of thermoplastics described above.
      • Thermosets are harder, more rigid/stiffer and not as easily bent or stretched, in fact they can be quite brittle and almost impossible to stretch (not very elastic!).
    • Note that thermosets type polymers can be formed at room temperature, heating may not be required.
      • Many super glues form this kind of structure.
    • However, you have to get it right first time because thermosetting polymers cannot be softened with heat and therefore cannot be stretched or re-shaped, but the advantage is that thermosets are much more heat resistant than thermoplastics.
    • But these cross-linked thermoset polymers are much more rigid (e.g. can't be stretched) and stronger material (though they can be brittle) and not as flammable as most thermoplastics.
    • On heating them strongly they do NOT melt, but tend to char, gradually giving off gases.
    • A simple diagram of the polymer molecules in the three different situation.

      • Thermoplastic: The polymer molecules tend to be randomly jumbled up, but no cross-linking bonds.

      • Fibres: Fibre molecules are thermoplastic molecules but manufactured in such a way to get the 'molecules more lined up' to increase intermolecular forces and the strength of the fibre, but no cross-linking bonds.

      • Thermosets: Their great strength and very rigid structure derives from the strong cross-links between the polymer strands. These cross-links are full chemical covalent bonds, NOT the much weaker intermolecular forces/bonding in thermoplastics.

        • In thermoplastics you have intermolecular bonding (weak attractive forces) between polymer molecules.

        • In thermosets you have intramolecular chemical bonding (very strong attractive forces) between the adjacent polymer molecule chains.

    • Heat resistant polymers are usually thermosets e.g. like melamine resin (plastic plates), but even thermoplastics like poly(propene) can be used in hot situations e.g. plastic electric kettles.

  • Melamine (used in furniture), Bakelite (was used for electrical fittings, a horrible brown colour but a good insulator, not used now?), Formica (table tops) and some super glues are examples of thermosetting polymers.
  • See also ....

Advanced Chemistry Page Index and Links

11B. More on Other Synthetic Polymers - macromolecules

SYNTHETIC FIBRES like NYLON and TERYLENE - condensation polymers

Condensation polymerisation involves linking lots of small monomer molecules together by eliminating a small molecule. This is often water from two different monomers, a H from one monomer, and an OH from the other, the 'spare bonds' then link up to form the polymer chain.

Condensation polymerisation involves monomers with two functional groups (one at each end of the molecule). When these types of monomers react they join together (polymerise), small molecules such as water are eliminated in the process, and so the reactions are called condensation reactions, hence the process is called condensation polymerisation.

The simplest polymers are made from two different monomers with two of the same functional groups on each monomer.

  • A polyester can be made from ethane diol (an alcohol with two hydroxy groups two -OH's) and hexanedioic acid (a carboxylic acid with two -COOH groups).
    • These are the two starting monomers prior to polymerisation and both must have a reactive group at each end.
    • Alcohols react with carboxylic acid to form esters with the elimination of water.
    • In this case the ester linkage is formed at both ends of each molecule with the elimination of water molecules.
    • Polyesters are condensation polymers because of how they are formed - by this condensation reaction that eliminates a small molecule to form the bond between the monomers..
    • Where n is the very large number of monomer molecules, the condensation polymerisation of ethane diol and hexanedioic acid can be represented as ...

n HO-CH2-CH2-OH + n HOOCCH2CH2CH2CH2COOH ===>-(-CH2-CH2-OOC-CH2CH2CH2CH2-COO-)n-  +  n H2O

or more simply: n HO-[][]-OH + n HOOC-[][][][]-COOH ==> -(-[][]-OOC-[][][][]-COO-)n-+  2n H2O

where n is a very large number !

  • Nylon (a polyamide) is formed by condensation polymerisation, the structure of nylon represented below where the rectangles represent the rest of the carbon chains in each unit.
  • Nylon is made polymerising a dicarboxylic acid and a diamine with the elimination of water.
  • n HOOC-[][][][]-COOH + n H2N-[][][][]-NH2 ==> -(-OC[][][][]-CONH-[][][][]-NH-)n-+  2n H2O
  • nylon (3 units etc.)
  • This is the same linkage (-CO-NH-) that is found in linked amino acids in naturally occurring macromolecules called proteins, where it is called the 'peptide' linkage.
    • Nylon-6,6 (c) doc b
  • Terylene (a polyester) is formed by condensation polymerisation and the simplified structure of Terylene can be represented as
  •  terylene  (3 units etc.).
  • However, above is a more accurate representation of the polyester Terylene, where you can see the ester linkage (COOC) more clearly, but this level of molecular structure is probably not needed at GCSE/IGCSE chemistry level.
  • This is the same kind of 'ester linkage' (-COOC-) found in fats which are combination of long chain fatty carboxylic acids and glycerol (alcohol with 3  -OH groups, a 'triol').
  • Terylene (a polyester) and nylon are good for making 'artificial' or 'man-made' fibres used in the clothing and rope industries.
    • In the manufacturing process the polymer chains are made to line up.
    • This greatly increases the intermolecular forces between the 'aligned' polymer molecules and strong fibre strands of the plastic can be made.
  • Although these are actually thermoplastic polymers, nylon and terylene can be drawn out into thin strong fibres for use in clothing.

  • Some important structure, strength and 1D, 2D and 3D dimension concepts are in the Chemical Bonding notes.
  • Advanced Chemistry Page Index and LinksNylon and polyester are typical synthetic fibres which have, in many cases, replaced cotton, silk and wool fabrics in the clothing industry.
    • They are cheap to make on an industrial scale compared to cotton from fields, silk from silkworms and wool from sheep.
    • As well as being cheaper, the physical properties of synthetic fibres have several advantages compared to their natural predecessors like cotton, silk and wool.
    • Compared to natural fibres, synthetic fibres tend to be ....
      • lighter - outdoor or indoor clothing,
      • more durable - harder tougher wearing fibres,
      • water-resistant - better water-proofed fabrics,
      • However, there are some disadvantages e.g.
    • The most common use of polyester today is called PET (for short!) and is used to make the plastic bottles for storing liquids in like soft drinks. PET is very useful because it is transparent, shatterproof and cheap!
      • Fine polyester fibres can be made into a variety of articles of clothing which are lighter and cheaper than traditional materials like wool.
      • Plastic bottles made from polyester can recycled and turned into fibres again and reused in clothing, are you wearing a plastic bottle!


11C. Examples of NATURAL POLYMERS, their structure, function and uses

  • A don't forget that silk fibres (strong fibre for fabrics), rubber (for tyres and elastic objects) are very useful natural polymers.
  • Silk has been used as a clothing and decorative fabric for thousands of years, and, like sheeps wool, is essentially a protein polymer material.

    • Synthetic man-made polymers like nylon and terylene where developed and designed to try and mimic silk's useful clothing properties, and nylon's excellent properties eg strength have meant it has found many and diverse applications. You need to read the nylon and terylene sections on this page.

  • Rubber has been used for centuries as a natural elastic polymer, but it has been replaced by synthetic polymers like neoprene.

  • Wood, an extremely useful construction material, and is mainly a polymer mixture of cellulose (a polymer of glucose) and lignin (with a rigid cross-linked structure).
  • The valuable crop of cotton (for fabrics) also has a molecular structure based on cellulose, in fact it is the purest form of cellulose that occurs naturally and forms strong useful fibres.
  • Starch, cellulose and sugars are all carbohydrate molecules (more detailed notes on carbohydrates).
    • Sugars are small molecules, but starch and cellulose are natural polymers of sugars based on the condensation polymerisation of small sugar molecules like glucose.
    • Starch and sugars are used in the food industry, starch being a polymer based on sugar.
  • Amino acids have two functional groups from which peptides and proteins are made.
    • This involves a condensation polymerisation in the biochemistry of living systems.
    • The carboxylic acid group -COOH and the amino or amine group -NH2
    • The simplest one is aminoethanoic acid (glycine) H2N-CH2-COOH
    • Proteins are naturally occurring polymers based on amino acids.
    • Amino acids can undergo condensation polymerisation via the two functional groups to form peptides, and all sorts of combinations of amino acids produce the huge variety of proteins found in living systems.
    • For glycine the condensation polymerisation to give a glycine peptide can be shown as ..
    • n H2N-CH2-COOH  ===>  -(NH-CH2-COO-)n-  +  2n H2O
    • where n is a very large number, with the elimination of 2n water molecules, one from each link at either end of the glycine monomer molecule.
    • The equation illustrates the structure if only one amino acid is used, in reality, proteins are very complex using a variety of around 20 different amino acids, each with its own unique structure, leading to lots of different proteins with their own unique structure. Think of all the different tissues in your own body!
  • DNA (deoxyribonucleic acid)
    • DNA is a very large molecule essential for life and the basis of genetic chemistry in living systems.
    • In a cells biochemistry the DNA encodes genetic instructions for the development and functioning of all living organisms and viruses.
    • Most DNA molecules are two polymer chains made from four different monomers called nucleotides.
    • Two strands of the DNA molecule are coiled together in the form of a double helix.
  • -


See also A survey of the properties and uses of a wide range of materials


Choosing a Plastic for a Particular Use (this section is repeated on the other GCSE polymer notes page)

How we use polymer compositions depends on their properties, some are quoted in the data table below

So, below is a decision making exercise on choosing a plastic for a particular job!

Note: NOT ALL the properties are necessarily relevant to make the decision.

At the moment A to F match questions (a) to (f) once only, but I may add further questions!

This exercise should provide a good challenge and discussion for a class, any feedback comments appreciated.

Polymer product Production cost Chemical resistance Melting point Strength (rigidity) Transparency can be made into fibres?
A high high high high good no
B low low high moderate poor no
C low low low low opaque yes
D low low low low poor no
E high low high very high opaque yes
F low high high high poor no

(a) Which plastic could be used as for disposable tableware like plates for hot meals or coffee cups?

(b) Which plastic could be used as a moving plastic component in a machine?

(c) Which plastic could used as containers for high volume production line of acids or alkalis?

(d) Which plastic could be used as laboratory volume measuring instrument e.g. a syringe or measuring cylinder

(e) Which plastic is suitable for clothing fabrics?

(f) Which plastic would be used for super-market carrier bags?

Answers near the end of the page

  • Plastics are widely used in the manufacture of cars and other road vehicles because they are cheap to make of varied composition for a wide variety of uses, they are light, durable and can be dyed any colour, they can be flexible or rigid and so can be used for e.g. used for internal fittings e.g. dashboard cover, floor covers (can be rubber too), door coverings, transparent and coloured covers over headlights and brake lights, and the insulating sheathing for all the electrical wiring.

  • See also A survey of the properties and uses of a wide range of materials

Multiple Choice Quizzes and Worksheets

KS4 Science GCSE/IGCSE m/c QUIZ on Oil Products (easier-foundation-level)

KS4 Science GCSE/IGCSE m/c QUIZ on Oil Products (harder-higher-level)

KS4 Science GCSE/IGCSE m/c QUIZ on other aspects of Organic Chemistry

and (c) doc b 3 linked easy Oil Products gap-fill quiz worksheets

ALSO gap-fill ('word-fill') exercises originally written for ...

... AQA GCSE Science (c) doc b Useful products from crude oil AND (c) doc b Oil, Hydrocarbons & Cracking etc.

... OCR 21st C GCSE Science (c) doc b Worksheet gap-fill C1.1c Air pollutants etc ...

... Edexcel 360 GCSE Science Crude Oil and its Fractional distillation etc ...

... each set are interlinked, so clicking on one of the above leads to a sequence of several quizzes

ALL my Advanced Level Organic Chemistry revision notes

Notes information to help revise KS4 Science Additional Science Triple Award Separate Sciences Chemistry revision notes for GCSE/IGCSE/O level Chemistry Revision-Information Study Notes for revising AQA GCSE Science AQA GCSE Chemistry, Edexcel GCSE Science, Edexcel GCSE Chemistry, OCR 21st Century Science Chemistry, OCR Gateway Science chemistry, WJEC/CBAC GCSE science-chemistry CCEA/CEA GCSE science-chemistry (and courses equal to US grades 8, 9, 10)

Answers to the Choosing a Plastic for a Particular Use Exercise in decision making

(a) Plastic B, to be disposable it must be cheap, chemical resistance doesn't matter (only in contact with food/drinks once), needs to be heat resistant, transparency doesn't matter?, needs to be reasonably rigid.

(b) Plastic E, firstly, it must be very strong to withstand the physical movement and friction in a working machine, it withstand heat from friction, chemical resistance need not be high, high cost acceptable for a specialised non-disposable part of a machine.

(c) Plastic F, needs to be reasonably cheap but heat and chemical resistant.

(d) Plastic A, it needs to be transparent to read the calibration marks accurately, it needs to be chemically and heat resistant to safe to use in the laboratory, it needs to be rigid to retain its accuracy, the high cost would be acceptable for a valuable measuring instrument in the laboratory, its not disposable.

(e) Plastic C, most important that it can be made into fibres, chemical and heat resistance is the responsibility of the owner/wearer!, needs to opaque or it becomes a 'see through'!

(f) Plastic D, the plastic needs to cheap, flexible and disposable (low cost), heat and chemical resistance are not important - responsibility of user!

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